Trifluoro-methanesulfonic acid 2-[benzyl-((E)-2-tributylstannanyl-pent-2-enoyl)-amino]-phenyl ester | 833461-95-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Trifluoro-methanesulfonic acid 2-[benzyl-((E)-2-tributylstannanyl-pent-2-enoyl)-amino]-phenyl ester
• CAS: 833461-95-3
• 化学式: C₃₁H₄₄F₃NO₄SSn
• 分子量: 702.466
• InChiKey: GGHDZDQNKPMJCF-UHFFFAOYSA-N

物化性质

• 沸点：
  634.7±65.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.17
• 重原子数：
  41.0
• 可旋转键数：
  17.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  63.68
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Trifluoro-methanesulfonic acid 2-[benzyl-((E)-2-tributylstannanyl-pent-2-enoyl)-amino]-phenyl ester 在 1,2,2,6,6-五甲基哌啶 、 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 palladium diacetate 、 copper(l) iodide 、 三(2-呋喃基)膦 、 (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl 作用下， 以 N-甲基吡咯烷酮 、 N,N-二甲基乙酰胺 为溶剂， 反应 24.0h， 生成 (S)-benzyl-3-prop-1-enyl-1,3-dihydro-3,3'-spiro[1,3-dioxolane]-1H'-[3,7']biindolyl-2,2'-2,2'-dione
  参考文献：
  名称：

  Enantioselective Synthesis of Six-Membered Palladacycles Having Metal-Bound Stereogenic Carbons:  Isolation and Reactivity of Palladacycles Containing Readily Accessible β-Hydrogens

  摘要：

  Five enantiopure palladacycles containing palladium bonded to a stereogenic carbon and an N-coordinated oxindole were synthesized by the reaction of alkenyl aryl triflates 2 and 9 with Pd(0) bisphosphine complexes. Two palladacyclic complexes, 3beta and 10alpha, were characterized by single-crystal X-ray crystallography. The reactivity of neutral palladacycles 3beta and 10beta was studied in detail. These unusual palladium alkyls, which have three accessible beta-hydrogens, are thermally stable at temperatures as high as 120 degreesC. At higher temperature, or at room temperature in the presence of weak acids, these complexes epimerize at the stereogenic carbon bonded to palladium. The mechanism of the acid-promoted epimerization was studied in detail. During this epimerization, cationic palladium alkyls 13/14 and 33 and cationic palladium hydride alkene complexes 31 and 32 are in rapid equilibrium.

  DOI：

  10.1021/ja045047p
• 作为产物：
  描述：

  三正丁基氢锡 、 Trifluoro-methanesulfonic acid 2-(benzyl-pent-2-ynoyl-amino)-phenyl ester 在 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 以91%的产率得到Trifluoro-methanesulfonic acid 2-[benzyl-((E)-2-tributylstannanyl-pent-2-enoyl)-amino]-phenyl ester
  参考文献：
  名称：

  Enantioselective Synthesis of Six-Membered Palladacycles Having Metal-Bound Stereogenic Carbons:  Isolation and Reactivity of Palladacycles Containing Readily Accessible β-Hydrogens

  摘要：

  Five enantiopure palladacycles containing palladium bonded to a stereogenic carbon and an N-coordinated oxindole were synthesized by the reaction of alkenyl aryl triflates 2 and 9 with Pd(0) bisphosphine complexes. Two palladacyclic complexes, 3beta and 10alpha, were characterized by single-crystal X-ray crystallography. The reactivity of neutral palladacycles 3beta and 10beta was studied in detail. These unusual palladium alkyls, which have three accessible beta-hydrogens, are thermally stable at temperatures as high as 120 degreesC. At higher temperature, or at room temperature in the presence of weak acids, these complexes epimerize at the stereogenic carbon bonded to palladium. The mechanism of the acid-promoted epimerization was studied in detail. During this epimerization, cationic palladium alkyls 13/14 and 33 and cationic palladium hydride alkene complexes 31 and 32 are in rapid equilibrium.

  DOI：

  10.1021/ja045047p